Head over Heels is a 2001 American romantic comedy-thriller film directed by Mark Waters. The film was panned by critics and failed to recover its modest $14 million budget. Plot Amanda Pierce (Monica Potter), a New York paintings conservator at the Metropolitan Museum of Art, has bad judgment in men, which becomes apparent when she finds her boyfriend cheating on her with a supermodel. She looks for a new apartment, and finds one with four struggling models: Jade (Shalom Harlow), Roxana (Ivana Miličević), Candi (Sarah O'Hare) and Holly (Tomiko Fraser). When Amanda discovers that Jim Winston (Freddie Prinze Jr.), a guy she likes, lives in the apartment across from hers, she starts spying on him to try to find his flaw. One night she sees him kill a woman, Megan O'Brien (Tanja Reichert). However, she is the only witness; and when the police arrive, they find no evidence of the crime. Annoyed by the police's lack of effort, Amanda and her new friends investigate Jim on their own. When Amanda confronts him, he turns out to be an undercover FBI agent, Bob Smoot, who was trying to gain a suspect's trust by staging his partner Megan's death. Amanda learns that Jim is investigating a Russian named Strukov (Jay Brazeau), who, under the alias of Halloran, has been smuggling money. He is also the client for whom Amanda has been privately restoring a painting. Strukov captures Jim, Amanda and her roommates; but they escape when Roxana seduces their Russian guard. They discover Strukov is actually smuggling diamonds. They go to a fashion runway, take down Strukov, and receive special commendations from the FBI. Jim asks Amanda if they can start over, but she refuses and he leaves. However, Amanda and Jim—going by his real name, Bob—"meet" again. He takes her up to his new apartment, from where they can see Amanda's model friends, who are obviously happy that things turned out so well for her. Cast Freddie Prinze Jr. as Jim Winston / FBI Special Agent Bob Smoot Monica Potter as Amanda Pierce Ivana Miličević as Roxana Milla Slasnakova Shalom Harlow as Jade Sarah O'Hare as Candi Tomiko Fraser as Holly Payton China Chow as Lisa Timothy Olyphant as Michael Tanja Reichert as Megan O'Brien Tanner as Hamlet the Great Dane Jay Brazeau as Mr. Halloran / Vadiim Strukov Stanley DeSantis as Alfredo Betty Linde as Polly Norma MacMillan as Gladys